


The Spot

by SupernaturalWinchester67



Series: SPN 2019 Kink Bingo [24]
Category: Supernatural
Genre: Bottom Dean Winchester, Dry Orgasm, F/M, Light Bondage, Light Dom/sub, Prostate Milking, Smut, Spanking, Vaginal Sex, dom reader
Language: English
Status: Completed
Published: 2019-11-23
Updated: 2019-11-23
Packaged: 2021-02-26 05:47:53
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 682
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21538483
Author URL: https://archiveofourown.org/users/SupernaturalWinchester67/pseuds/SupernaturalWinchester67
Summary: Dean gets his favorite punishment served out to him…A/N: Fulfills the Prostate Milking square of SPN 2019 Kink Bingo
Relationships: Dean Winchester/You
Series: SPN 2019 Kink Bingo [24]
Series URL: https://archiveofourown.org/series/1247360
Kudos: 41





	The Spot

“I’m sorry, mistress,” said Dean. You stared down at him, Dean blinking up with wide eyes. “I…I didn’t mean to come.”

“Dean. I can tell when it’s an actual accident and when you were actively seeking an orgasm out and this was most certainly the later. I hope you enjoyed it,” you said, rolling off the bed, going to the box of toys sitting on the desk. “On your stomach.”

He was restrained but loosely, more than enough give for him to comfortably roll over. You picked up Dean’s most favorite and most hated toy, crawling back in bed, making sure he knew what you’d picked out.

“Do you know what’s going to happen now, Dean?” you asked. He mumbled into the mattress and you slapped his bottom.

“Ah, yes! Milking. Bad boys don’t get to come. They get milked,” he said quickly.

“That’s right. Now since you just came, I don’t expect it to take long to get you nice and empty,” you said.

“Yes mistress,” he said.

“And when I’m all done?”

“I’ll come dry. Bad boys come dry if they’re good,” he said.

“Yes. Yes they do,” you said. Dean groaned, burying his face in the sheets while you opened up the lube. You drenched a finger and pressed it to Dean’s hole, pushing inside with little resistance. It stretched quickly and you added another, Dean biting his bottom lip. “No. I want to hear you.”

He released his lip and you waited a few moments before switching out your fingers for the lubed up prostate massager. It wasn’t very thick, less than two of your fingers to be honest, but the knobby end would rub Dean mercilessly.

It took little time to find his prostate, Dean gasping when you zeroed in on it.

“Stay still, Dean. This is a punishment after all.”

The toy moved over his prostate quickly, pressing up against it, Dean doing his best to stay there and take it.

“Oh shit, shit,” said Dean. You saw a dark spot start to form under him, Dean letting out quiet whimpers and moans.

“Knees,” you said. Dean hazily complied, resting back on his heels, back bowed forward, legs spread. You watched the cum leak from his cock as you went back to rubbing, Dean gasping and squirming in place. “Good boy. This is how you make a good boy, isn’t it, Dean?”

“Yes, mistress,” he groaned, cock giving one last spurt of cum. You continued with the motion for another minute, Dean scrunching up his face as nothing more came out.

“There we go. Good boy,” you said. You set the toy aside and grabbed his hips, rolling him to his back. He arched his back when you climbed on his cock and rode him hard. “Make me come, Dean. Make me come and I’ll let you come again.”

He planted his feet and thrust up, a tiny yelp escaping you putting a smile on his face. He did it again as you found a rhythm with him, grinding down on his cock until you were coming around him. He sucked in a breath as he throbbed and you knew he was coming dry inside you, Dean throwing his head back against the bed.

You got your breath back before you climbed off, giving Dean a kiss and starting to untie him.

“Good boy, Dean. You did so good,” you said, kissing his shoulder, Dean smiling at you. “You know, I think you’ve been getting in trouble so much lately just so I milk you.”

“Whatever gave you that idea,” he teased.

“Might have to take to regularly doing it outside the heavier stuff. Maybe I’ll start milking you every day, turn you into a good boy that has to work for the right to come properly, hm? Would you like that?”

“Fuck yeah,” he said, grabbing your cheek and kissing you. “Maybe we try that out next week, see if you can break my bad boy streak.”

“Oh I think with regular milking, you’ll turn into the best little sub there ever was, Dean.”


End file.
